Ethanol → HCID 68567766, compound

HRID 1454279Notes

Reaction equation

HRID 1454279 reaction equation
[Na].[CH3:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)COS(C)(=O)=O)[CH2:6]2.O.[CH2:27](O)[CH3:28]>>[CH3:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH:20]=[CH:25][C:24]1[CH:23]=[CH:22][CH:21]=[CH:28][CH:27]=1)[CH2:6]2

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 962WaterHCID 5360545SodiumHCID 20800560HCID 20800560, compound

Product 1

HCID 68567766HCID 68567766, compound

Procedure

Under argon sodium metal (0.58 g, 24.37 mmol) was slowly added to anhydrous ethanol. After all the sodium was reacted methanesulfonic acid 2-(5-methyl-1-oxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-ethyl ester (5.61 g, 16.25 mmol) dissolved in ethanol was added to the reaction mixture and the solution was stirred for 6 h at room temp. The reaction was poured into water and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was used in the next step without further purification. Yield 3.64 g.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe solvent removed under reduced pressure
  7. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-d376c19368cc4d88af3b96418c422b92
Source dataset
uspto-grants-2009_01
Patent number
US07479495B2

Reaction notes

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